I don't spend much of my time entering sweepstakes nowadays. It seems like I'm not so lucky to win anything and, quite honestly, I get sick of entering in my information to get lots of spam. Sometimes though entering sweepstakes pays off, like when you actually win free stuff or get some good coupons. Freebies 4 mom posted some current sweepstakes & the odds of your winning something. It's a very useful list if you'd like to enter some of these:

Subway (83,000+ details here)
Hanes (20,000+ enter each Wednesday, details here)
Mamma Mia (10,000+ details here)
Colgate (10,000+ details here)
Dove (9,000+ details here)
Kraft (5,000+ details here)
Lipton (5,000+ details here)
Teas' (3,000+ details here)
Totino's (2,000+ details here)
Oreo (2,000+ details here)
Publix (2,000+ only for residents of AL, GA, FL, SC, TN details here)
Jelly Belly (2,000+ details here)
Batman (2,000+ details here)
Summer of Savings (1,000+ details here)
Tony's Pizza (1,000+ details here)
Wyndham (1,000+ skip to instant win + coupons, details here)
Wish-Bone (1,000+ details here)
WALL*E's (1,000+ details here) ends July 28
Pilgrim's Pride (1,000+ details here)
International Delight (1,000+ details here)
Spraychel (1,000+ details here)